Molecules 2012, 17(10), 11554-11569; doi:10.3390/molecules171011554
Article

Design and Synthesis of an 18F-Labeled Version of Phenylethyl Orvinol ([18F]FE-PEO) for PET-Imaging of Opioid Receptors

János Marton 1 email and Gjermund Henriksen 2,3,* email
1 ABX Advanced Biochemical Compounds Biomedizinische Forschungsreagenzien GmbH, Heinrich-Glaeser-Strasse 10-14, D-01454 Radeberg, Germany 2 Oslo PET-Centre, Norsk Medisinsk Syklotronsenter AS, N-0027 Oslo, Norway 3 Institute of Basic Medical Sciences, Group of Pharmaceutical Radiochemistry, University of Oslo, Postboks 1110 Blindern, N-0317 Oslo, Norway
* Author to whom correspondence should be addressed.
Received: 13 July 2012; in revised form: 10 September 2012 / Accepted: 11 September 2012 / Published: 28 September 2012
PDF Full-text Download PDF Full-Text [263 KB, Updated Version, uploaded 1 October 2012 15:18 CEST]
The original version is still available [263 KB, uploaded 28 September 2012 15:08 CEST]
Abstract: The semisynthetic oripavine derivative phenethyl orvinol (PEO), a full agonist at opioid receptors (OR), is an attractive structural motif for developing 18F-labeled PET tracers with a high degree of sensitivity for competition between endogenous and exogenous OR-ligands. The target cold reference compound 6-O-(2-fluoroethyl)-6-O-desmethylphenylethyl orvinol (FE-PEO) was obtained via two separate reaction routes. A three-step synthesis was developed for the preparation of a tosyloxyethyl precursor (TE-TDPEO), the key precursor for a direct, nucleophilic radiofluorination to yield [18F]FE-PEO. The developed radiosynthesis provides the target compound in relevantly high yield and purity, and is adaptable to routine production.
Keywords: opioid receptors; PET; agonist; 18F-fluorination; automated radiosynthesis

Supplementary Files

Article Statistics

Click here to load and display the download statistics.

Cite This Article

MDPI and ACS Style

Marton, J.; Henriksen, G. Design and Synthesis of an 18F-Labeled Version of Phenylethyl Orvinol ([18F]FE-PEO) for PET-Imaging of Opioid Receptors. Molecules 2012, 17, 11554-11569.

AMA Style

Marton J, Henriksen G. Design and Synthesis of an 18F-Labeled Version of Phenylethyl Orvinol ([18F]FE-PEO) for PET-Imaging of Opioid Receptors. Molecules. 2012; 17(10):11554-11569.

Chicago/Turabian Style

Marton, János; Henriksen, Gjermund. 2012. "Design and Synthesis of an 18F-Labeled Version of Phenylethyl Orvinol ([18F]FE-PEO) for PET-Imaging of Opioid Receptors." Molecules 17, no. 10: 11554-11569.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert